Azo dyestuffs and process of making same



Patented May 13, 1924. i

1,493,577 PATENT OFFICE.

HERMANN WAGNER, OF I- IOECHST-ON-THE-MAIN, GERMANY, ASS IGNOR, TOCHEMISCHE FABRIK GRIESHEIM-ELEKTRON, F FRANKFORT-QN-THE-MAIN, GERMANY, A. COR- PORATION O'F GERMANY.

AZO DYES'I'UFFS AND PROCESS OF MAKING SAME.

No Drawing.

T 0 all whoirt it may concern: 1

Be it known that I, HERMANN VAGNER, a citizenof Germany, residing at Hoechst-onthe Main, Germany, have invented certain new and useful Improvements in Azo Dyestuffs and Processes of h/[aking Same, of which the following is a specification.

I have found that dyestuffs of excellent tastness to kier-boiling are'obtained by combining any diazo-compound withthe 4- chloro-3-toluidide or the 4-bromo-3-toluidide'of 2.3-oxynaphthoic acid. The, fastnesS to kier-boiling of such dyestuffs as compared with that of dyestuffs of similar composition is of such superiority, that they are predestined to open new methods in the manufacture of colored fabrics The dyestufi s containing halogen in both components are distinguishedv by particularly ex-' cellent qualities.

-The following examples illustrate my invention:

The material is treated with- 1. Padding f liquorr23 grams 2.3-oxynaphthoic acid4-chloro-3-toluidide,20 grams para soap PN, '60 ccm. caustic soda lye of 22 B., made up to 1 litre with boiling water then it is dried and printed with the following Printing paste: 14.1 grams 6-chloro-2- toluidine, 26 grams hydrochloric acid otQQ" B., 170 grams hot wateiycool'with ice, and add 7 grams sodium nitrite dissolved in 50 ccm.- of water, made up to EGO-grams; thicken this solution with 480 grams trag- .acanth (60:1000) and before use add- 20 grams sodium acetate, giving 1 kilo of printing paste. A bright scarlet tint is ob tained on the fibre.

2. Padding liquor as described in Example 1 and Printing paste: 14.1 grams 5-chloro-2- toluidine. and the other ingredients as'specified in Example 1i in this case a red tint with a bluish hue is obtained.

5. Padding liquor as' described in EX Application filed June 30, 1922. Serial No. 572,039.

toluidine and the other ingredients as specified in Example 1; in this case a deep red tint is obtained.

5. Padding liquor as described in Example 1 and a Printing paste: 18.6 grams 4- bromo-2- toluidine and the other ingredients as specitied in Example 1.

6. Padding liquor as described in Example 1. I r

Printing paste: 15.7 grams 4-chloro-2- anisidine and the other ingredients as specified in Example 1; in this case a claret-red tint with a yellow hue is obtained.

7. Padding liquor. 27, grams 2.3-oxynaphthoic acid-4-bromo-3-toluidide, 20 grams para soap PN. grams caustic soda lye of 22 B. made up to 1. litre with boiling water.

Printing paste: 14.1 grams G-chloro-Q- toluidine andthe other ingredients as specitied in Exampleyl; in this case a bright scarlet tint is obtained.

8. Padding. liquor as described in Ex ample 7.

Printing paste: 14.1 grams 5-chloro-2- toluidine and the other ingredients as specified in Example 1; in this case a red tint is obtained.

.9. Padding liquor as described in Example 7.

Printing paste: 14.1 grams 4ehloro-2-- toluidine and the other ingredients as specified in Example 1: in this case a red tint with a faint blue hue is obtained.

-J0.. Padding liquor as described in Example 7. 0

Printing paste: 15.7 grams 4-chl0ro-2 anisidine-and the other ingredients as'speci fied in Example 1: in this case a claret-red tint with a yellow hue is obtained.

.1]. Padding liquor as described in Example v7.

Printing paste .7 14.1 grams of 4-chloro-3- toluidine and the other ingredients as specitied in Example 1.

12. Padding liquor as described in Example 7.

Printing paste: 18.6 grams 4-bromo-2- toluidine and the other ingredients as specified in Example 1.

All prints obtained by means of the above mentioned solutions and printing pastes possess very great fastness to kier-boiling and to light.-

Having now described my invention what the halogenated .mononuclear methyl and I claim is: methoxy substituted aromatic hydrocarbons As new produets, the azo dyestufi's of the and X stands for oneof the ha1ogens, ch1ogeneral formula I v rine and bromine, which products yield, 5 5 N=NR when-gredueed with stannous chloride and hydrochloric acid, a halogenated substi- OH x. tuted aromatic amine and a toluidide of the OO NH 1-am1no-2-oxy-3-naphtho1c acld.

\ In testimony whereof I afiix 'my signs. 20 CHB n ture. wherein R stands for one of the residues of v HERMANN WAGNER. 

